5-Diethyl-amino-2-{(E)-[(3-iodo-phen-yl)imino]-meth-yl}phenol.

The title Schiff base, C(17)H(19)IN(2)O, is not planar, displaying a dihedral angle of 34.9 (2)° between the two aromatic rings. The mol-ecular conformation allows the formation of a strong intra-molecular O-H⋯N hydrogen bond with graph-set motif S(6) between the hy-droxy group and the imine N atom.

Related literature

For Schiff base tautomerism, see: Cohen et al. (1964 ▶); Hadjoudis et al. (1987 ▶). For the biological properties of Schiff bases, see: Dao et al. (2000 ▶). For related structures, see: Gül, Ağar & Işık (2007 ▶); Gül, Erşahin, Ağar & Işık (2007 ▶); Pekdemir et al. (2012 ▶); Yüce et al. (2004 ▶); Demirtaş et al. (2011 ▶). For the classification of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H19IN2O

M = 394.24

Orthorhombic,

a = 6.6999 (6) Å

b = 15.248 (2) Å

c = 16.1195 (15) Å

V = 1646.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.95 mm−1

T = 296 K

0.49 × 0.34 × 0.21 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.451, T max = 0.603

6072 measured reflections

3225 independent reflections

2417 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.074

S = 0.86

3225 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.63 e Å−3

Absolute structure: Flack (1983 ▶), 1355 Friedel pairs

Flack parameter: −0.02 (3)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022556/bh2429sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022556/bh2429Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022556/bh2429Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H19IN2O	Dx = 1.590 Mg m−3
Mr = 394.24	Melting point: 394 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8061 reflections
a = 6.6999 (6) Å	θ = 1.8–28.1°
b = 15.248 (2) Å	µ = 1.95 mm−1
c = 16.1195 (15) Å	T = 296 K
V = 1646.7 (3) Å3	Prism, yellow
Z = 4	0.49 × 0.34 × 0.21 mm
F(000) = 784

Stoe IPDS II diffractometer	3225 independent reflections
Radiation source: fine-focus sealed tube	2417 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.8°
rotation method scans	h = −6→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −15→19
Tmin = 0.451, Tmax = 0.603	l = −20→20
6072 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0337P)2] where P = (Fo2 + 2Fc2)/3
S = 0.86	(Δ/σ)max = 0.002
3225 reflections	Δρmax = 0.57 e Å−3
190 parameters	Δρmin = −0.63 e Å−3
0 restraints	Absolute structure: Flack (1983), 1355 Friedel pairs
0 constraints	Flack parameter: −0.02 (3)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	0.5355 (9)	0.7994 (3)	0.3130 (3)	0.0424 (14)
C2	0.6547 (9)	0.8639 (3)	0.2779 (3)	0.0438 (13)
H2	0.7869	0.8699	0.2946	0.053*
C3	0.5784 (8)	0.9186 (3)	0.2188 (3)	0.0411 (13)
C4	0.3846 (10)	0.9108 (4)	0.1905 (4)	0.0539 (16)
H4	0.3353	0.9477	0.1494	0.065*
C5	0.2675 (12)	0.8468 (4)	0.2254 (4)	0.0648 (16)
H5	0.1361	0.8409	0.2077	0.078*
C6	0.3395 (9)	0.7908 (4)	0.2860 (4)	0.0513 (15)
H6	0.2573	0.7478	0.3085	0.062*
C7	0.5263 (10)	0.7053 (4)	0.4284 (3)	0.0463 (16)
H7	0.3934	0.7205	0.4366	0.056*
C8	0.6183 (8)	0.6397 (4)	0.4808 (4)	0.0398 (14)
C9	0.5079 (9)	0.5976 (4)	0.5432 (4)	0.0470 (14)
H9	0.3765	0.6148	0.5522	0.056*
C10	0.5856 (9)	0.5330 (4)	0.5909 (3)	0.0474 (15)
H10	0.5071	0.5067	0.6314	0.057*
C11	0.7872 (8)	0.5048 (3)	0.5794 (3)	0.0396 (12)
C12	0.8970 (8)	0.5476 (4)	0.5182 (3)	0.0429 (13)
H12	1.0285	0.5305	0.5091	0.052*
C13	0.8187 (8)	0.6140 (4)	0.4706 (3)	0.0382 (14)
C14	1.0628 (11)	0.4029 (4)	0.6072 (4)	0.0602 (17)
H14A	1.1138	0.3722	0.6555	0.072*
H14B	1.1530	0.4512	0.5956	0.072*
C15	1.0651 (14)	0.3412 (6)	0.5345 (5)	0.098 (3)
H15A	1.1984	0.3200	0.5259	0.147*
H15B	1.0204	0.3715	0.4858	0.147*
H15C	0.9779	0.2926	0.5455	0.147*
C16	0.7536 (12)	0.3977 (4)	0.6930 (3)	0.0594 (15)
H16A	0.6713	0.4420	0.7194	0.071*
H16B	0.8452	0.3752	0.7345	0.071*
C17	0.6208 (11)	0.3235 (5)	0.6640 (6)	0.085 (2)
H17A	0.5497	0.2997	0.7105	0.127*
H17B	0.7012	0.2785	0.6392	0.127*
H17C	0.5273	0.3454	0.6239	0.127*
I1	0.76828 (6)	1.01529 (2)	0.16772 (2)	0.05438 (13)
N1	0.6279 (7)	0.7428 (3)	0.3703 (3)	0.0431 (11)
N2	0.8680 (7)	0.4386 (3)	0.6273 (3)	0.0478 (12)
O1	0.9360 (6)	0.6522 (3)	0.4129 (2)	0.0532 (11)
H1	0.8727	0.6905	0.3888	0.080*

	U11	U22	U33	U12	U13	U23
C1	0.056 (3)	0.032 (3)	0.039 (3)	0.004 (3)	0.001 (2)	−0.006 (2)
C2	0.048 (3)	0.044 (3)	0.039 (3)	0.000 (3)	0.000 (2)	0.002 (2)
C3	0.042 (3)	0.037 (3)	0.044 (3)	0.002 (2)	0.011 (2)	0.004 (2)
C4	0.061 (4)	0.049 (4)	0.051 (4)	0.000 (3)	−0.017 (3)	0.008 (3)
C5	0.049 (4)	0.062 (3)	0.084 (4)	−0.002 (4)	−0.015 (4)	0.008 (3)
C6	0.051 (4)	0.041 (3)	0.061 (4)	−0.006 (3)	−0.008 (3)	0.005 (3)
C7	0.055 (4)	0.043 (4)	0.040 (3)	0.008 (3)	0.006 (3)	−0.008 (3)
C8	0.047 (3)	0.032 (3)	0.040 (3)	−0.003 (3)	0.007 (3)	−0.001 (3)
C9	0.043 (3)	0.047 (4)	0.051 (4)	−0.003 (3)	0.011 (3)	0.003 (3)
C10	0.046 (3)	0.051 (4)	0.045 (3)	0.000 (3)	0.009 (2)	0.004 (3)
C11	0.041 (3)	0.036 (3)	0.041 (2)	0.000 (3)	−0.002 (2)	−0.0006 (17)
C12	0.040 (3)	0.042 (3)	0.046 (3)	0.001 (2)	0.008 (3)	−0.002 (3)
C13	0.046 (4)	0.032 (3)	0.037 (3)	−0.006 (2)	0.007 (2)	−0.002 (2)
C14	0.063 (4)	0.056 (4)	0.061 (4)	0.010 (3)	−0.007 (3)	0.013 (3)
C15	0.108 (7)	0.089 (6)	0.098 (7)	0.025 (5)	0.021 (5)	−0.012 (5)
C16	0.064 (4)	0.061 (3)	0.054 (3)	−0.001 (5)	0.002 (4)	0.018 (2)
C17	0.072 (5)	0.069 (5)	0.114 (6)	−0.019 (4)	0.003 (5)	0.024 (5)
I1	0.0585 (2)	0.05387 (18)	0.05074 (17)	−0.0006 (2)	0.0024 (2)	0.01511 (17)
N1	0.054 (3)	0.036 (2)	0.039 (2)	−0.001 (2)	0.004 (2)	0.003 (2)
N2	0.050 (3)	0.052 (3)	0.041 (2)	0.003 (2)	0.005 (2)	0.011 (2)
O1	0.051 (3)	0.060 (3)	0.048 (3)	0.008 (2)	0.015 (2)	0.013 (2)

C1—C2	1.388 (7)	C11—N2	1.381 (7)
C1—C6	1.390 (8)	C11—C12	1.393 (7)
C1—N1	1.407 (7)	C12—C13	1.374 (7)
C2—C3	1.365 (7)	C12—H12	0.9300
C2—H2	0.9300	C13—O1	1.349 (6)
C3—C4	1.381 (8)	C14—N2	1.450 (8)
C3—I1	2.114 (5)	C14—C15	1.503 (10)
C4—C5	1.373 (8)	C14—H14A	0.9700
C4—H4	0.9300	C14—H14B	0.9700
C5—C6	1.384 (8)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—N1	1.292 (7)	C16—N2	1.449 (7)
C7—C8	1.446 (8)	C16—C17	1.512 (9)
C7—H7	0.9300	C16—H16A	0.9700
C8—C9	1.404 (8)	C16—H16B	0.9700
C8—C13	1.409 (8)	C17—H17A	0.9600
C9—C10	1.354 (8)	C17—H17B	0.9600
C9—H9	0.9300	C17—H17C	0.9600
C10—C11	1.430 (9)	O1—H1	0.8200
C10—H10	0.9300
C2—C1—C6	118.8 (5)	C13—C12—H12	118.7
C2—C1—N1	116.7 (5)	C11—C12—H12	118.7
C6—C1—N1	124.3 (5)	O1—C13—C12	118.7 (5)
C3—C2—C1	120.1 (5)	O1—C13—C8	121.0 (6)
C3—C2—H2	119.9	C12—C13—C8	120.2 (5)
C1—C2—H2	119.9	N2—C14—C15	114.7 (6)
C2—C3—C4	122.0 (5)	N2—C14—H14A	108.6
C2—C3—I1	118.2 (4)	C15—C14—H14A	108.6
C4—C3—I1	119.8 (4)	N2—C14—H14B	108.6
C5—C4—C3	117.6 (5)	C15—C14—H14B	108.6
C5—C4—H4	121.2	H14A—C14—H14B	107.6
C3—C4—H4	121.2	C14—C15—H15A	109.5
C4—C5—C6	121.9 (6)	C14—C15—H15B	109.5
C4—C5—H5	119.0	H15A—C15—H15B	109.5
C6—C5—H5	119.0	C14—C15—H15C	109.5
C5—C6—C1	119.5 (6)	H15A—C15—H15C	109.5
C5—C6—H6	120.3	H15B—C15—H15C	109.5
C1—C6—H6	120.3	N2—C16—C17	114.0 (5)
N1—C7—C8	120.3 (6)	N2—C16—H16A	108.8
N1—C7—H7	119.8	C17—C16—H16A	108.8
C8—C7—H7	119.8	N2—C16—H16B	108.8
C9—C8—C13	117.3 (6)	C17—C16—H16B	108.8
C9—C8—C7	120.6 (5)	H16A—C16—H16B	107.6
C13—C8—C7	122.0 (6)	C16—C17—H17A	109.5
C10—C9—C8	122.5 (6)	C16—C17—H17B	109.5
C10—C9—H9	118.8	H17A—C17—H17B	109.5
C8—C9—H9	118.8	C16—C17—H17C	109.5
C9—C10—C11	120.6 (5)	H17A—C17—H17C	109.5
C9—C10—H10	119.7	H17B—C17—H17C	109.5
C11—C10—H10	119.7	C7—N1—C1	121.0 (5)
N2—C11—C12	122.1 (5)	C11—N2—C16	121.0 (5)
N2—C11—C10	121.2 (4)	C11—N2—C14	120.2 (5)
C12—C11—C10	116.7 (5)	C16—N2—C14	118.6 (5)
C13—C12—C11	122.6 (5)	C13—O1—H1	109.5
C6—C1—C2—C3	1.1 (8)	C10—C11—C12—C13	0.2 (8)
N1—C1—C2—C3	176.8 (5)	C11—C12—C13—O1	179.6 (5)
C1—C2—C3—C4	−1.7 (8)	C11—C12—C13—C8	−1.9 (9)
C1—C2—C3—I1	−179.9 (4)	C9—C8—C13—O1	−178.9 (5)
C2—C3—C4—C5	1.5 (9)	C7—C8—C13—O1	2.5 (8)
I1—C3—C4—C5	179.7 (4)	C9—C8—C13—C12	2.7 (8)
C3—C4—C5—C6	−0.8 (9)	C7—C8—C13—C12	−175.9 (5)
C4—C5—C6—C1	0.3 (9)	C8—C7—N1—C1	172.9 (5)
C2—C1—C6—C5	−0.4 (8)	C2—C1—N1—C7	152.9 (5)
N1—C1—C6—C5	−175.8 (5)	C6—C1—N1—C7	−31.6 (8)
N1—C7—C8—C9	−179.0 (6)	C12—C11—N2—C16	177.3 (5)
N1—C7—C8—C13	−0.4 (9)	C10—C11—N2—C16	−2.5 (8)
C13—C8—C9—C10	−1.9 (9)	C12—C11—N2—C14	−8.6 (8)
C7—C8—C9—C10	176.7 (6)	C10—C11—N2—C14	171.6 (5)
C8—C9—C10—C11	0.3 (9)	C17—C16—N2—C11	85.1 (7)
C9—C10—C11—N2	−179.6 (5)	C17—C16—N2—C14	−89.0 (7)
C9—C10—C11—C12	0.6 (7)	C15—C14—N2—C11	−76.5 (8)
N2—C11—C12—C13	−179.5 (5)	C15—C14—N2—C16	97.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.577 (6)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.577 (6)	147